CAS: 174810-09-4; N,N'-((1R,2R)-Cyclohexane-1,2-Diyl)Bis(2-(Diphenylphosphino)-1-Naphthamide)

该化合物是1-Naphthacolboxamide和1R,2,2R)-环己二胺衍生的一双双双螺旋,其主要结构特征包括硬性环己烷脊柱和二苯磷基,这加强了非对称催化的选择性立体.这种链条在过渡性金属催化反应(如氢化和交叉结合)中特别有用,因为它能够形成稳定的金属复合体,具有高度的对应性控制.氯化萘会进一步有助于-粉化相互作用,改善子质结合.其定义明确的(R,R)配置确保了抗逆转录选择性合成的一贯性功能,使其成为生产药物和精美化学中光活性中间体的可靠选择.

结构式图片

上下游产品

CAS号20439-47-8 (1R,2R)-(-)-1,2-环己二胺 | CAS号178176-80-2 2-联苯基膦基-1-萘甲酸 | CAS号947-65-9 2-羟基-1-萘酸甲酯 | CAS号178176-78-8 2-二苯基膦-1-萘甲酸甲酯 | CAS号200573-11-1 2-三氟甲磺酰氧-1-萘甲酯

合成工艺路线路线简述

  • 合成目标产物 (1R,2R)-(+)-1,2-Diaminocyclohexane-N,N'-Bis(2-Diphenylphosphino-1-Naphthoyl) 主要起始原料 Methyl 2-Hydroxy-1-Naphthoate
  • (文献来源)合成步骤主要原料 Methyl 2-Hydroxy-1-Naphthoate
2-羟基-1-萘酸甲酯置于吡啶,二(氰基苯)二氯化钯,Barium Hydroxide octahydrate,Diphenyl Phosphorochloridite,三乙胺体系中,用 甲醇,二氯甲烷,甲苯 用作溶剂,化学反应 82.0H,反应生成(1R,2R)-(+)-1,2-二氨基环己烷-N,N'-双(2-苯基膦-1-萘酰基)
参考文献:二烯单环氧化物的动态动力学不对称转化:乙烯基甘氨醇,氨己烯酸和乙胺丁醇的实用不对称合成
标题:二烯单环氧化物的动态动力学不对称转化:乙烯基甘氨醇,氨己烯酸和乙胺丁醇的实用不对称合成
摘要:在丁二烯单环氧化物的背景下探索了使用钯催化的不对称烯丙基烷基化 (Aaa) 进行动态动力学不对称转化 (Dykat) 的能力.通过将两种对映异构体转化为单一对映异构体产品,这种市售但外消旋的四碳结构单元的多功能性得到显着增强.该概念是在以邻苯二甲酰亚胺为氮源合成乙烯甘氨醇的背景下进行的.该项目的成功需要钯配体的新设计,其中引入了额外的构象限制.因此,乙烯甘氨醇的邻苯二甲酰亚胺衍生物以接近定量的收率获得,Ee 为 98%,在结晶时提高到 >99%.这种保护形式的乙烯基甘氨醇的一步合成提供了标题化合物的简短实用合成.Vigabatrin 只需要四个步骤,乙胺丁醇需要六个步骤.现有合成的中间体...
Doi:10.1021/ja000547D

专利信息


专利号:US-8288566-B2
优先权日:2008-11-17
标 题 :Enantioselective synthesis of γ-amino-αβ-unsaturated carboxylic acid derivatives
发明人:ACEMOGLU MURAT; PFALTZ ANDREAS; SCHAERER CLAUDE
权利人:ACEMOGLU MURAT; PFALTZ ANDREAS; SCHAERER CLAUDE; NOVARTIS AG
摘要:Provided is an enantioselective, palladium-catalyzed method for the preparation of γ-amino-α,β-unsaturated carboxylic acid derivatives having the formulas II, III, VII and VIII:

专利号:US-2017369519-A1
优先权日:2016-06-27
标 题 :Methods for the stereoselective preparation of apiose derivatives from allylic alcohol compounds and allene compounds using catalytic asymmetric synthesis
发明人:RHEE YOUNG HO; KIM MIJIN; KANG SOYEONG
权利人:POSTECH ACADEMY-INDUSTRY FOUND
摘要:The present invention relates to a method for the stereoselective preparation of apiose derivatives from allylic alcohol compounds and allene compounds using catalytic asymmetric synthesis. The method for the stereoselective preparation of apiose derivatives of the present invention is based on the catalytic asymmetric synthesis from allylic alcohol compounds and allene compounds in the presence of a metal catalyst, so that apiose derivatives can be produced stereoselectively, with high yield, with high optical purity regardless of the types of substituents of the compounds. The method of the invention can also be used for the preparation of oligosaccharides including monosaccharides, disaccharides, and polysaccharides or various compounds including apiose derivatives because the method can minimize the production of by-products without using an activating group, unlike the conventional method for the preparation of adipose derivatives.

专利号:US-10450282-B2
优先权日:2015-08-06
标题:Stereospecific process for 3-heterocyclylcycloaliphatic-1,2-diols
发明人:OHLMEYER MICHAEL; ZAWARE NILESH; KASTRINSKY DAVID
权利人:ICAHN SCHOOL MED MOUNT SINAI
摘要:A process for the stereoselective synthesis of chiral 3-heterocyclyl-1,2-dihydroxy cyclohexanes is disclosed. The process involves reacting a tricyclic nitrogenous heterocycle with an allyl carbonate in the presence of a chiral palladium catalyst followed by oxidation of the olefinic bond to provide 3-heterocyclyl-1,2-dihydroxy cyclohexanes, cyclopentanes and corresponding alicyclic heterocycles. Also disclosed are methods for converting the heterocyclyl-1,2-dihydroxy cyclohexanes to 2-amino-6-(heteroaryl)cyclohexanols (and related cyclic compounds).

专利号:US-2012330030-A1
优先权日:2008-11-17
标 题 :Enantioselective Synthesis of y-amino-a, B-unsuturated carboxylic acid derivatives

专利号:US-2011263873-A1
优先权日:2008-11-17
标题:Enantioselective Synthesis of y-amino-alpha beta-unsaturated carboxylic acid derivatives

专利号:JP-2009544589-A
优先权日:2006-07-15
标题 :Regioselective palladium-catalyzed synthesis of benzimidazole and azabenzimidazole
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合成参考文献


摘要:Pitts, C. R.; Lectka, T., Science of Synthesis Knowledge Updates, (2017) 2, 379.
摘要:Tius, M. A., Science of Synthesis Knowledge Updates, (2022) 1, 474.
摘要:Ye, Z.-S., Science of Synthesis Knowledge Updates, (2021) 2, 341.
摘要:Tius, M. A., Science of Synthesis Knowledge Updates, (2022) 1, 462.
摘要:Crawley, M. L., Science of Synthesis: Stereoselective Synthesis, (2011) 3, 427.
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